Cationic iridium-catalyzed enantioselective activation of secondary sp 3 C-H bond adjacent to nitrogen atom

Shiguang Pan, Yusuke Matsuo, Kohei Endo, Takanori Shibata

    Research output: Contribution to journalArticle

    58 Citations (Scopus)

    Abstract

    A cationic Ir(I)-tolBINAP complex catalyzed an enantioselective C-C bond formation, which was initiated by secondary sp 3 C-H bond cleavage adjacent to nitrogen atom. A wide variety of 2-(alkylamino)pyridines and alkenes were selectively transformed into the corresponding chiral amines with moderate to almost perfect enantiomeric excesses. Alkynes were also investigated as coupling partners. The effect of alkyl structure in substrates and directing groups were studied. This transformation represents the first example of a highly enantioselective C-H bond activation of a methylene group, not at allylic or benzylic position.

    Original languageEnglish
    Pages (from-to)9009-9015
    Number of pages7
    JournalTetrahedron
    Volume68
    Issue number44
    DOIs
    Publication statusPublished - 2012 Nov 4

    Fingerprint

    Pyridines
    Iridium
    Alkynes
    Alkenes
    Amines
    Nitrogen
    Chemical activation
    Atoms
    Substrates

    Keywords

    • C-H activation
    • Enantioselective
    • Heterocycle
    • Iridium

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Cationic iridium-catalyzed enantioselective activation of secondary sp 3 C-H bond adjacent to nitrogen atom. / Pan, Shiguang; Matsuo, Yusuke; Endo, Kohei; Shibata, Takanori.

    In: Tetrahedron, Vol. 68, No. 44, 04.11.2012, p. 9009-9015.

    Research output: Contribution to journalArticle

    Pan, Shiguang ; Matsuo, Yusuke ; Endo, Kohei ; Shibata, Takanori. / Cationic iridium-catalyzed enantioselective activation of secondary sp 3 C-H bond adjacent to nitrogen atom. In: Tetrahedron. 2012 ; Vol. 68, No. 44. pp. 9009-9015.
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